EP1339432A1 - Composes d'inclusion moleculaires constitues de polysaccharides lineaires insolubles dans l'eau fabriques de maniere biocatalytique et d'acides gras ou de derives d'acides gras - Google Patents
Composes d'inclusion moleculaires constitues de polysaccharides lineaires insolubles dans l'eau fabriques de maniere biocatalytique et d'acides gras ou de derives d'acides grasInfo
- Publication number
- EP1339432A1 EP1339432A1 EP01994752A EP01994752A EP1339432A1 EP 1339432 A1 EP1339432 A1 EP 1339432A1 EP 01994752 A EP01994752 A EP 01994752A EP 01994752 A EP01994752 A EP 01994752A EP 1339432 A1 EP1339432 A1 EP 1339432A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- molecular inclusion
- fatty acids
- water
- inclusion compound
- linear
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000004676 glycans Chemical class 0.000 title claims abstract description 57
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 57
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 57
- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 37
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 33
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 33
- 239000000194 fatty acid Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000002537 cosmetic Substances 0.000 claims abstract description 6
- 235000013373 food additive Nutrition 0.000 claims abstract description 4
- 239000002778 food additive Substances 0.000 claims abstract description 4
- 235000013376 functional food Nutrition 0.000 claims abstract description 4
- 235000015872 dietary supplement Nutrition 0.000 claims abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 3
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 claims abstract 5
- 238000000034 method Methods 0.000 claims description 14
- 229920001503 Glucan Polymers 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 150000002634 lipophilic molecules Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 108090000637 alpha-Amylases Proteins 0.000 claims description 8
- 102000004139 alpha-Amylases Human genes 0.000 claims description 7
- 229940024171 alpha-amylase Drugs 0.000 claims description 7
- 239000004014 plasticizer Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 4
- -1 fatty acid esters Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- 235000021588 free fatty acids Nutrition 0.000 claims description 2
- 238000000265 homogenisation Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000012360 testing method Methods 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 239000006041 probiotic Substances 0.000 claims 1
- 230000000529 probiotic effect Effects 0.000 claims 1
- 235000018291 probiotics Nutrition 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 abstract description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 34
- 229920002472 Starch Polymers 0.000 description 22
- 235000019698 starch Nutrition 0.000 description 20
- 239000008107 starch Substances 0.000 description 18
- 235000021314 Palmitic acid Nutrition 0.000 description 17
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- 229920000856 Amylose Polymers 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 238000010668 complexation reaction Methods 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000306 component Substances 0.000 description 6
- 239000003094 microcapsule Substances 0.000 description 6
- 238000000944 Soxhlet extraction Methods 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 229930091371 Fructose Natural products 0.000 description 4
- 239000005715 Fructose Substances 0.000 description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 210000002429 large intestine Anatomy 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000016709 nutrition Nutrition 0.000 description 4
- 230000035764 nutrition Effects 0.000 description 4
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000011514 reflex Effects 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 108010033764 Amylosucrase Proteins 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000002083 X-ray spectrum Methods 0.000 description 3
- 230000002210 biocatalytic effect Effects 0.000 description 3
- 230000036983 biotransformation Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002016 disaccharides Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 235000012041 food component Nutrition 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000002772 monosaccharides Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 108010065511 Amylases Proteins 0.000 description 2
- 102000013142 Amylases Human genes 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 229920001218 Pullulan Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000019418 amylase Nutrition 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000001427 coherent effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000007824 enzymatic assay Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 235000019423 pullulan Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- AFENDNXGAFYKQO-VKHMYHEASA-N (S)-2-hydroxybutyric acid Chemical compound CC[C@H](O)C(O)=O AFENDNXGAFYKQO-VKHMYHEASA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N Glycerol trihexadecanoate Natural products CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- 108010001483 Glycogen Synthase Proteins 0.000 description 1
- 108700023372 Glycosyltransferases Proteins 0.000 description 1
- 102000051366 Glycosyltransferases Human genes 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 206010067997 Iodine deficiency Diseases 0.000 description 1
- 108010028688 Isoamylase Proteins 0.000 description 1
- 229920000057 Mannan Polymers 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 241000588660 Neisseria polysaccharea Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 108010073135 Phosphorylases Proteins 0.000 description 1
- 102000009097 Phosphorylases Human genes 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004373 Pullulan Substances 0.000 description 1
- 229920000294 Resistant starch Polymers 0.000 description 1
- 108010039811 Starch synthase Proteins 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229940025131 amylases Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 201000004050 brachyolmia-amelogenesis imperfecta syndrome Diseases 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000002153 concerted effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000005428 food component Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 108700014210 glycosyltransferase activity proteins Proteins 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 210000001822 immobilized cell Anatomy 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 235000006479 iodine deficiency Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- LUEWUZLMQUOBSB-GFVSVBBRSA-N mannan Chemical class O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H](O[C@@H](O)[C@@H](O)[C@H]3O)CO)[C@@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O LUEWUZLMQUOBSB-GFVSVBBRSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000021140 nondigestible carbohydrates Nutrition 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000021254 resistant starch Nutrition 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
Definitions
- the present invention relates to molecular inclusion compounds from biocatalytically prepared, water-insoluble, linear polysaccharides and from fatty acids or their derivatives, processes for their preparation and their use.
- Microcapsules are either in finely divided dispersions in which the material to be encapsulated is embedded in a sponge-like matrix (e.g. R94-9400419), or in structures in which the material to be encapsulated is not penetrated by the capsule material, but only surrounded (e.g. Arshady et al. 1990, Polymer Eng. Sci., 30 (15), 905-914 and 915-924).
- the compound to be encapsulated is part of the multimolecular aggregates. It is also known that starch components such as amylose and amylopectin can also be used to form the above microcapsules.
- microcapsules primarily serve to protect the encapsulated material against external influences (e.g. heat, UV light, oxidation), but can also make a significant contribution to easier processing (e.g. flowability, stickiness, conversion of liquid products into solid products).
- Another application of the microcapsules is oral application while influencing sensory properties.
- native starches can be used to form microcapsules (MK).
- starches with a high proportion of resistant starches (high RS content) are used, which are only fermentatively degraded in the large intestine and not, as usual, by pancreatic amylase in the stomach and small intestine.
- complex compounds of the iodine-starch complex type have also been described, in which one or more iodine or fatty acid molecules are embedded in a starch helix (cf. FIG. 1). This complex is referred to below as the molecular inclusion compound.
- Helical iodine-starch complexes and their use for medical and pharmaceutical application are described, for example, by Gehnt and Eskin in US Pat. No. 5,955,101.
- WO 94/17676 describes a composition of hydrolyzed starch as a matrix for incorporated lipophilic compounds.
- a combination of molecular inclusion and dispersion is proposed in DE 44 11 414.
- a product for the enteral supply of fatty acids is disclosed in which these are present in the product in a proportion of at least 10%.
- the fatty acid is finely dispersed in a plasticized starch matrix, some of the fatty acids being at least partially enclosed in an amylose helix.
- amylose helix it is not clear what the corresponding percentage of fatty acid molecules molecularly included in the amylose helix is.
- Molecular inclusion compounds are therefore known which are based on native and thus branched, water-soluble starch or their degradation products and in which, according to common, professional knowledge, a maximum of 4.6% by weight of fatty acid, based on the starch content, can be incorporated as a molecular inclusion compound (also: loading) (see also Example 4 and Krüger et al., Monthly Bull. Brauwiss. (1984) 37 (12) pp. 505-512). Fanta et al. describe the complexation (loading) of 4.6% by weight myristic acid in amylose-rich starch (Carbohydr. Polym. (1999) 38 (1) pp. 1-6). However, materials and processes that would allow a molecular inclusion of significantly higher amounts of fatty acids (higher loading) would be desirable.
- Molecular inclusion compounds are particularly well suited for use in pharmaceutical preparations, as functional foods, in cosmetic preparations and as food additives, and as food supplements, since the included compounds are very good, for example, against molecular influences such as e.g.
- the fields of application of such molecular inclusion compounds also depend very much on the properties of the materials used for the inclusion.
- the materials used are ⁇ -amylase resistant, so that the molecular inclusion compounds according to the invention are only digested in the large intestine. This can prevent the enzymatic / hydrolytic degradation of the molecular inclusion compound from occurring faster, based on the entire digestion process. It is particularly advantageous if the lipophilic molecules present in the interior of the molecular inclusion compounds are only released in the large intestine, so that they can be directly absorbed by the cells of the intestinal wall, without first being enzymatically involved, for example, by pancreatic enzymes split or modified. As a result, the bioavailability of the compounds can be increased in a particularly favorable manner.
- a further object of the present invention was to provide molecular inclusion compounds and processes for their production, in which the materials used for the inclusion have new properties which open up new fields of application or special advantages in use for molecular inclusion compounds. It was also an object of the present invention to provide improved molecular inclusion compounds and processes for their preparation which, owing to the materials used, can be used as a constituent of human or veterinary compositions, as a food and feed constituent and for cosmetic applications.
- a molecular inclusion compound characterized in that it consists of at least (a) a biocatalytically produced, linear, water-insoluble polysaccharide and (b) one (one) or more (more) fatty acid (s) or fatty acid derivative (s) ) consists.
- An object of the present invention is therefore monomolecular inclusion compounds from biocatalytically produced, water-insoluble, linear polysaccharides and helically complexed lipophilic molecules, e.g. Fatty acids or their esters, the amount of helically complexed lipophilic compound being at least 5% by weight, based on the polyglucan used.
- the amount of helically complexed lipophilic compound is preferably at least 7% by weight, based on the polysaccharide used, particularly preferably more than 9% by weight, based on the polysaccharide used, very particularly preferably more than 10% by weight, based on the polysaccharide used.
- linear, water-insoluble polysaccharides are homogenized in a mixture with a lipophilic compound and processed to form a homogeneous matrix. Any unbound excess of the lipophilic compound is then removed by extraction.
- a plasticizer can also be added. Homogenization can be brought about, for example, by extrusion. It is clear to the person skilled in the art that further, for example taste-improving, appearance-influencing or, in general, processability-influencing substances can be added.
- Preferred plasticizers according to the invention are odorless, colorless, light, cold and heat resistant, only slightly or not at all hygroscopic, water-resistant, not harmful to health, difficult to ignite and as little volatile as possible, neutral reaction, miscible with polymers and auxiliaries and have good gelling behavior on. In particular, they should be compared to the used components have compatibility, gelling ability and softening effectiveness.
- plasticizers examples include water, polyalcohols such as ethylene glycol, glycerol, propanediol, erythritol, maitol, sorbitol, polyvalent alkanoic acids such as maleic acid, succinic acid, adipic acid, polyvalent hydroxyalkanoic acids such as lactic acid, 2-hydroxybutyric acid, citric acid, malic acid, dimethyl or other solvents, urea for strength.
- polyalcohols such as ethylene glycol, glycerol, propanediol, erythritol, maitol, sorbitol
- polyvalent alkanoic acids such as maleic acid, succinic acid, adipic acid
- polyvalent hydroxyalkanoic acids such as lactic acid, 2-hydroxybutyric acid, citric acid, malic acid, dimethyl or other solvents, urea for strength.
- plasticizers are preferably used in a proportion of 2% by weight to 50% by weight, based on the polysaccharide component of the mixture according to the invention.
- fragrance or aroma substances, binders etc. can be added if, for example, a cosmetic or pharmaceutical use or a use as a food or nutritional component is intended.
- the degree of loading of native starch in palmitic acid which cannot be washed out with chloroform is 2-3% by weight. Surprisingly, this proportion increases to 7.7% by weight in the molecular inclusion compound according to the invention using biocatalytically prepared, linear and water-insoluble 1,4- ⁇ -D-polyglucan as polysaccharide.
- the fatty acid is only released from the molecular inclusion compound after degradation by suitable enzymes or chemical hydrolysis under suitable conditions and can then be reisolated.
- Linear, water-insoluble polysaccharides in the context of the present invention are polysaccharides which are built up from monosaccharides, disaccharides or other monomeric units in such a way that the monosaccharides, disaccharides or other monomeric units are always linked to one another in the same way.
- Each basic unit or building block defined in this way has exactly two links, one each to a different monomer. From that except for the two basic units that form the beginning and the end of the polysaccharide. These basic units have only one link to another monomer. With three links on a basic unit (covalent bonds) one speaks of a branch.
- Linear, water-insoluble polysaccharides in the sense of the invention have no branches or at most only to a minor extent, so that the very small branch fractions cannot be detected using conventional analytical methods such as, for example, 13 C or 1 H NMR spectroscopy.
- DAß German Pharmacopoeia, Scientific Publishing House mbH, Stuttgart, Govi-N erlag GmbH, Frankfurt, 9th edition, 1987
- Water-insoluble polysaccharides preferred according to the invention can therefore be assigned to class 4 of the DASS, that is to say that a saturated solution of the polysaccharide at room temperature and normal pressure comprises about 30 to 100 parts by volume of solvent, ie water, per part by weight of substance (1 g substance per 30-100 ml water).
- Water-insoluble polysaccharides which are more preferred according to the invention can be assigned to class 5 of the DAB, ie that a saturated solution of the polysaccharide at room temperature and normal pressure comprises about 100 to 1000 parts by volume of solvent, ie water, per part by weight of substance (1 g substance per 100-1000 ml water).
- even more preferred water-insoluble polysaccharides can be assigned to class 6 of the DAB, ie that a saturated solution of the polysaccharide at room temperature and normal pressure comprises about 1000 to 10000 parts by volume of solvent, ie water, per part by weight of substance (1 g substance per 1000-10000 ml water).
- the most preferred water-insoluble polysaccharides can be assigned to class 7 of the DAB, that is to say that a saturated solution of the polysaccharide at room temperature and normal pressure comprises about 10,000 to 100,000 parts by volume of solvent, ie water, per part by weight of substance (lg substance per 10000-100000 ml water).
- sparingly soluble to practically insoluble polysaccharides especially very sparingly soluble to practically insoluble polysaccharides, are preferred.
- It is preferably water-insoluble poly- ⁇ -1,4-D-glucan.
- linear, water-insoluble polysaccharides which have been produced in a biocatalytic (synonym: biotransformer) or a fermentative process are preferred.
- Linear polysaccharides produced by biocatalysis in the context of this invention means that the linear polysaccharide is produced by catalytic reaction of basic monomeric units such as oligomeric saccharides, for example mono- and / or disaccharides, using a so-called biocatalyst, usually an enzyme , is used under suitable conditions.
- Biocatalysis can be carried out with living, growing cells, with cells in the stationary state, with immobilized cells, with isolated or genetically engineered soluble or immobilized enzymes, in a single or multi-phase system.
- Linear polysaccharides from fermentations are, in the parlance of the present invention, linear polysaccharides which have been modified by fermentative processes using organisms which occur in nature, such as fungi, algae or bacteria, or using organisms which are not found in nature with the aid of genetic engineering methods of general definition natural organisms such as fungi, algae or bacteria can be obtained or can be obtained with the help of fermentative processes.
- linear polysaccharides according to the present invention can also be other polyglucans or other linear polysaccharides such as pullulans, pectins, mannans or polyfructans.
- linear polysaccharides for the preparation of the molecular inclusion compounds described in the present invention can also be obtained from the reaction of further non-linear polysaccharides by treating non-linear polysaccharides containing branches with an enzyme in such a way that they are used to cleave the Branching occurs, so that linear polysaccharides are present after their separation.
- enzymes can be, for example, amylases, iso-amylases, Act gluconohydrolases or pullulanases.
- the polysaccharides according to the invention should always be strictly linear.
- the polysaccharide used is 1,4- ⁇ -D-polyglucan.
- the 1,4- ⁇ -D-polyglucan is preferably produced by means of a biocatalytic (biotransformatory) process with the aid of polysaccharide synthases, starch synthases, glycosyltransferases, -1,4-glucantransferases, glycogen synthases, amylosucrases or phosphorylases.
- the molecular weights Mw of the linear polysaccharides used according to the invention can vary within a wide range from 10 3 g / mol to 10 7 g / mol.
- molecular weights Mw of 10 4 g / mol to 10 5 g / mol, in particular 2 ⁇ 10 4 g / mol to 5 ⁇ 10 4 g / mol are preferred.
- the ⁇ -amylase-resistant polysaccharides according to the invention can be characterized in that the 1,4- ⁇ -D-polyglucans are chemically modified in a manner known per se.
- 1,4- ⁇ -D-polyglucans may have been chemically modified by etherification or esterification in the 2-, 3- or 6-position.
- the person skilled in the art is sufficiently familiar with this chemical modification; see. for example the following literature:
- an RS content is understood to mean the content of ⁇ -amylase-resistant polysaccharides as it is according to the method of Englyst et al. (Classification and measurement of nutritionally important starch fractions, European Journal of Clinical Nutrition, 46 (Suppl. 23) (1992) 33-50).
- the molecular inclusion compounds described in the present invention have a high degree of resistance to ⁇ -amylase compared to native starch.
- the ⁇ -amylase-resistant inclusion compounds according to the invention are characterized in that an RS content according to Englyst is at least 30, preferably 50, particularly preferably 75 and very particularly preferably 95% by weight ,
- biocatalytically produced, linear and water-insoluble polysaccharides which can be used according to the invention have a whole series of features both of native strength and of those described in the prior art Distinguish enzymatic "debris products" of native starch. A summary of such differences is given in Table 1 below.
- the inventors mentioned above currently assume that the surprisingly high binding capacity of the inclusion compounds according to the invention compared to inclusion compounds from the prior art cannot be attributed to a single one of these substance characteristics, but rather the sum of these Properties, possibly the strict linearity of the molecules according to the invention and the lack of phosphate esters and the high water insolubility in their entirety are responsible for the fact that the inclusion compounds according to the invention have such surprisingly favorable properties. Since the linear 1,4-D-polyglucan can be a more resistant form compared to the native starch (RS> 30%), this has advantages in the oral application of compounds which have their effect only after the passage of the Should ignite stomach and small intestine.
- lipophilic agents can only be released specifically in the large intestine.
- lipophilic substances which can be used according to the invention are saturated fatty acids or unsaturated fatty acids, so-called PUFAs.
- PUFAs (English: Poly-Unsaturated Fatty Acids; German: polyunsaturated fatty acids) are understood in the parlance of the present invention as fatty acids with a chain length of more than 12 carbon atoms with at least two double bonds (see Table 2).
- the fatty acids can be used both in the form of the free fatty acids, as fatty acid esters, as physiologically acceptable salts of the fatty acids, as triglycerides or in the form of other derivatives.
- these fatty acids can be protected against premature digestion in the digestive system.
- polysaccharide component of the mixture according to the invention can also be a mixture of different biocatalytically produced, water-insoluble and linear polysaccharides.
- Figure 1 shows a schematic representation of the molecular inclusion compound.
- A Process of binding a fatty acid into the polysaccharide helix;
- B Fully stored fatty acid.
- Figure 2 shows X-ray spectra for poly- ⁇ -l, 4-D-glucan with 35% glycerol (1) and additionally 2.5% (2), 5% (3) and 10% (4) palmitic acid.
- the biotransformation supernatant is denatured at 95 ° C. After cooling to room temperature, centrifugation was carried out again. The clear supernatant was frozen at -70 ° C and thawed at 4 ° C for 3 days. The precipitate thus generated was frozen at -70 ° C and freeze-dried.
- 39.5 g of the solid are washed with water for 30 min with stirring at room temperature, frozen at -70 ° C. and freeze-dried.
- the fructose and sucrose content is determined after dissolving the solid in DMSO by a coupled enzymatic assay according to Stitt et al. (Meth. Enzym., 174 (1989) 518-552) and is 2.27 mg fructose per 100 mg solid.
- the sucrose content is below the detection limit.
- a mixture of 200g poly- ⁇ -l, 4-D-glucan (material from Example 1), 70g glycerol and 5g, 10g, 20g or 30g palmitic acid (corresponds to 2.5%, 5%, 10% or 15% based on the weight fraction of the polyglucan) are initially charged and homogenized in the extruder at 170 ° C. and 100 rpm. Samples are taken from the product after cooling. The melting peaks of the samples are determined using DSC (Digital Scanning Calorimetry). The degree of complexation Kx is then determined with the aid of a Soxhlet extraction (chloroform, 48h) by dissolving out the uncomplexed palmitic acid.
- Table 3 shows results of a Soxhlet extraction in which native starch (purified potato starch) was used instead of poly- ⁇ -1,4-D-glucan in the sample preparation according to Example 1.
- Table 3 Results of DSC and Soxhlet extraction
- Example 3 The samples described in Example 3 were subjected to an X-ray structure analysis.
- X-ray spectra for poly- ⁇ -l, 4-D-glucan with 35% glycerol (1) and 5 additionally 2.5% (2), 5% (3) and 10% (4) palmitic acid are shown in FIG. 2. It can be seen that the spectrum for the pure, plasticized poly- ⁇ -1,4-D-glucan (1) from the amorphous halo, the three larger peaks at 13.7, 15.5 and 21.1 ° 2 ⁇ , as well as some smaller peaks. The reflections at 13.7 and 21.1 ° are characteristic of the simple helix of V-amylose, a structure type that is typical of complex starches.
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Abstract
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10059726 | 2000-11-30 | ||
| DE10059726 | 2000-11-30 | ||
| PCT/EP2001/013971 WO2002043768A1 (fr) | 2000-11-30 | 2001-11-29 | Composes d'inclusion moleculaires constitues de polysaccharides lineaires insolubles dans l'eau fabriques de maniere biocatalytique et d'acides gras ou de derives d'acides gras |
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| Publication Number | Publication Date |
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| EP1339432A1 true EP1339432A1 (fr) | 2003-09-03 |
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| EP01994752A Withdrawn EP1339432A1 (fr) | 2000-11-30 | 2001-11-29 | Composes d'inclusion moleculaires constitues de polysaccharides lineaires insolubles dans l'eau fabriques de maniere biocatalytique et d'acides gras ou de derives d'acides gras |
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| Country | Link |
|---|---|
| US (1) | US20040048829A1 (fr) |
| EP (1) | EP1339432A1 (fr) |
| JP (1) | JP2004518777A (fr) |
| WO (1) | WO2002043768A1 (fr) |
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| JPWO2006082968A1 (ja) * | 2005-02-07 | 2008-06-26 | 江崎グリコ株式会社 | α−1,4−グルカンを含有する吸着剤およびその製造方法 |
| US20110256261A1 (en) * | 2007-08-10 | 2011-10-20 | Univ Iowa State Res Found | Resistant food starches and methods related thereto |
| JP5572323B2 (ja) * | 2009-03-04 | 2014-08-13 | 備前化成株式会社 | 包摂反応においてホスト化合物の選択性を高める低分子多糖類、およびそれを用いた苦味成分および臭い成分を包摂する方法 |
| AR087157A1 (es) | 2011-06-20 | 2014-02-26 | Gen Biscuit | Galletita saludable |
| CN114522635B (zh) * | 2022-01-24 | 2023-08-25 | 华南理工大学 | 一种具有可控释放肉桂醛的抗菌微胶囊及其制备方法 |
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| RU2201963C2 (ru) * | 1994-05-18 | 2003-04-10 | Плант Тек Биотехнологи Гмбх Форшунг Унд Энтвиклунг | ПОСЛЕДОВАТЕЛЬНОСТЬ ДНК (ВАРИАНТЫ), РЕКОМБИНАНТНАЯ ДНК, ПРОТЕИН, СПОСОБ ПОЛУЧЕНИЯ ПРОТЕИНА, СПОСОБ ПОЛУЧЕНИЯ МИКРООРГАНИЗМОВ, СПОСОБ ПОЛУЧЕНИЯ КЛЕТОК ГРИБА, СПОСОБ ПОЛУЧЕНИЯ ЛИНЕЙНЫХ α-1,4-ГЛЮКАНОВ И/ИЛИ ФРУКТОЗЫ И СПОСОБ ПОЛУЧЕНИЯ ЛИНЕЙНЫХ α-1,4-ГЛЮКАНОВ И/ИЛИ ФРУКТОЗЫ IN VITRO |
| JP2913010B2 (ja) * | 1995-03-09 | 1999-06-28 | 農林水産省食品総合研究所長 | 有機溶媒可溶化リパーゼを用いる糖質−脂肪酸複合体の製造方法 |
| DE19852826A1 (de) * | 1998-11-17 | 2000-05-18 | Aventis Res & Tech Gmbh & Co | Poly(alpha-1,4-D-Glucan) |
-
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- 2001-11-29 JP JP2002545738A patent/JP2004518777A/ja active Pending
- 2001-11-29 EP EP01994752A patent/EP1339432A1/fr not_active Withdrawn
- 2001-11-29 WO PCT/EP2001/013971 patent/WO2002043768A1/fr not_active Ceased
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- 2003-05-29 US US10/448,245 patent/US20040048829A1/en not_active Abandoned
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| See references of WO0243768A1 * |
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| WO2002043768A1 (fr) | 2002-06-06 |
| JP2004518777A (ja) | 2004-06-24 |
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